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Which edition? A lot of the good tools are version-specific, although there are also plenty of generally useful tools.
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BryantAug 24 '10 at 17:51

Yeah, I'd like to see this question rephrased to include an edition. Already, the comments are scattering across 3.5e and 4e. Any answer that recommends an edition-specific tool without mentioning which edition it works with will confuse people.
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Adam DrayAug 25 '10 at 16:25

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This question looks like it would invite lists-of-lists answers; I'm therefore voting to close it unless it can be narrowed down.
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GMJoeApr 9 '14 at 7:28

12 Answers
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I've used ProFantasy's products for creating cities, continents, etc. They are excellent products and full featured though they can get a little pricey.

An alternative for creating dungeon maps is using a vector drawing program such as Inkscape (free) or Xara (pay). You can create objects that you can quickly cut and paste for repeated patterns. Since it's vector based these can easily be accurately resized for different scales. You can even print out pages for use with miniatures.

Most of all I've depended on spreadsheets software (Excel, OpenOffice Calc) to create templates for character sheets. A lot of these templates are available online or you can create your own. Ultimately you can print them out if you're not using a computer at your gaming session or view them online.

I've normally stored game notes and adventures in Word or OpenOffice Writer, but I've been considering using a wiki (such as Twiki) or a small database (such as sqlite) to store some of this data.

When playing DD3.0-3.5 I had written a perl script that helped me generate NPCs. It was quite a bit of work, but proved quite useful. It generated full stats, spells, skills, etc.

We're using Obsidian Portal in our current game; it allows us all to take notes of what happened, have character sheets visible, and share wiki entries, and generally manage the shared pool of imagination our game accumulates. I recommend it.

I had a DM in 3.5 that used DM Genie, and it seemed like a good tool, although I didn't look under the hood much.

A word of advice sparked by that experience though: don't let the computer become a barrier between you and the players or disrupt the flow of play. We spend a lot of time watching our DM click his mouse in silence, and he tended to value what he had in the computer over our own memories. Don't do that.

I wanted a very simple, fast loading wiki without dice rolling, initiative tracking, rule referencing, tactical maps, chat capabilities, and so on. I ended up running a wiki for every campaign I played in with the software I know. Other people are free to use Campaign Wiki as well, even though it's far simpler than Obsidian Portal.

Spreadsheet: I use OpenOffice Calc, but Excel works. It's good for tracking combat and for character sheets. Especially when you track gear weight and cost.

Outlining Text Editor: Emacs with Org-mode for me. Other people use things like Word, but I like Emacs Org-mode because the syntax matches up with PMWiki, so I can just paste my notes in directly and they're already formatted properly.

Campaign Wiki: I use PMWiki, for a number of reasons. A couple of big ones are that the syntax matches up with Org-mode well, and the other is that it has a mobile-friendly skin.

Random generators: Sometimes you just need something you haven't had time to prepare. Place or NPC names are common, as are dungeons, treasure, traps, and... just about everything, really. I've actually run entire sessions off of random generators. Google is your friend on this one.

Automated die roller: Take your pick. I wrote my own to use from a Linux command line. It helps to be able to roll large numbers of dice quickly and without digging around for (say) 30d6 when the wizard goes nova. Excel macros are good for this too.

If you're playing 4E, there are two programs that are indispensable to me. Masterplan (for building adventures/encounters, in inCombat, for initiative/status tracking. If you're going to have a computer at your table during the game, it's a handy program for keeping track of all the moving pieces. Both are Adobe Air apps

For 4e, Character Builder and the D&D compendium are pretty darn good. I'm not a fan of the way they were created, but I do think they are excellent tools.

Outside of those programs, whatever you use to keep notes and if you use a computer to play music for the mood, I'm not sure a computer is the best way to keep the game flowing. Some players (and DMs) are easily distracted by the computers.

I'm currently developing an open-source platform-independent desktop suite to address my own needs in this area. You can check out the GitHub repository here. Right now it handles dice rolling and I'm currently working on the combat tracking. It tracks initiative, HP, position, and some statuses. It comes with a sample blank battle grid where each square is labelled with its coordinates so inputting them into the program is simple and doesn't require tedious math or counting. Traps, spells, and powers are also planned tracking features. It's a work in progress and gets updated frequently.